PtCl2-catalyzed cyclization of o-diethynylbenzene derivatives triggered by intramolecular nucleophilic attack

Synthetic Communications

Volumn 41, Issue 7, 2011, Pages 1077-1087

  Miki, Koji ^a   Kuge, Hiroyuki ^a   Umeda, Rui ^a   Sonoda, Motohiro ^a   Tobe, Yoshito ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Cyclization; Dihydronaphthofuran; Lewis acid; Nucleophilic addition; o diethynylbenzene

Indexed keywords

BENZENE DERIVATIVE; FURAN DERIVATIVE; O DIETHYNYLBENZENE DERIVATIVE; PLATINUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CYCLIZATION; NONHUMAN; NUCLEOPHILICITY; SUBSTITUTION REACTION;

EID: 79952566695     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911003797817     Document Type: Article

References (22)

1. For reviews, see (a) Wang, K. K. Cascade radical cyclization via biradicals generated from enediynes, enyne-allenes, and enyne-ketenes. Chem. Rev. 1996, 96, 207-222;
2. (b) Basak, A.; Mandal, S.; Bag, S. S. Chelation-controlled Bergman cyclization: Synthesis and reactivity of enediynyl ligands. Chem. Rev. 2003, 103, 4077-4094.
3. (a) Grisson, J. W.; Calkins, T. L.; Egan, M. Synthetic studies of the tandem enediynemono- and bis-radical cyclizations. J. Am. Chem. Soc. 1993, 115, 11744-11752;
4. (b) Grisson, J. W.; Calkins, T. L.; Huang, D.; McMillen, H. High temperature radical cyclization anomalies in the tandem enediyne-bis-radical cyclization. Tetrahedron 1994, 50, 4635-4650;
5. (c) Chow, S.-Y.; Palmer, G. J.; Bowles, D. M.; Anthony, J. E. Perylene synthesis by the parallel cycloaromatization of adjacent endiynes. Org. Lett. 2000, 2, 961-963;
6. (d) Bowles, D. M.; Palmer, G. J.; Landis, C. A.; Scott, J. L.; Anthony, J. E. The Bergman reaction as a synthetic tool: Advantages and restrictions. Tetrahedron 2001, 57, 3753-3760;
7. (e) Scott, J. L.; Pakin, S. R.; Anthony, J. E. Radical-induced cycloaromatization: Routes to fluoranthenes and acephenanthrylenes. Synlett 2004, 161-164. (Pubitemid 38067819)
8. Landis, C. A.; Payne, M. M.; Eaton, D. L.; Anthony, J. E. Tellurium-mediated cycloaromatization of acyclic endiynes under mild conditions. J. Am. Chem. Soc. 2004, 126, 1338-1339.
9. (a) Wang, Y.; Finn, M. G. An organometallic diradical cycloaromatization reaction. J. Am. Chem. Soc. 1995, 117, 8045-8046;
10. (b) Ohe, K.; Kojima, M.-A.; Yonehara, K.; Uemura, S. Rhodium(I)-catalyzed cycloaromatization of acyclic 3-ene-1,5-diynes. Angew. Chem. Int. Ed. 1996, 35, 1823-1825;
11. (c) Manabe, T.; Yanagi, S.-I.; Ohe, K.; Uemura, S. New examples of 1,6- and 1,7-hydrogen transfer promoted by an a-silyl group in rhodium(I)-catalyzed radical reactions of acyclic enediynes. Organometallics 1998, 17, 2942-2944;
12. For reviews, see (d) König, B. Changing the reactivity of enediynes by metal-ion coordination. Eur. J. Org. Chem. 2000, 381-385;
13. (e) Trost, B. M.; McClory, A. Metal vinylidenes as catalytic species in organic reactions. Chem. Asian J. 2008, 3, 164-194.
14. (a) Wu, M.-J.; Lee, C.-Y.; Lin, C.-F. A route to 5-substituted dibenzofurans by anionic cycloaromatization of 2-(6-substituted 3-hexen-1,5-diynyl)phenyl tert-butyldimethyl ethers and related molecules. Angew. Chem. Int. Ed. 2002, 41, 4077-4079;
15. (b) Wu, M.-J.; Lin, C.-F.; Lu, W.-D. Anionic cycloaromatization of 1-aryl-3-hexen-1,5-diynes initiated by methoxide addition: Synthesis of phenanthridinones, benzo[c]phenanthridinones, and biaryls. J. Org. Chem. 2002, 67, 5907-5912.
16. (a) Utimoto, K. Palladium-catalyzed synthesis of heterocycles. Pure Appl. Chem. 1983, 55, 1845-1852;
17. (b) Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. Preparation of furans from alkynols utilyzing palladium-catalyzed intramolecular addition of alcohols to acetylene as a key reaction. Tetrahedron 1985, 41, 3655-3661.
18. Kuge, H.; Miki, K.; Sonoda, M.; Tobe, Y. Synthesis of dihydronaphthofuran derivatives via tandem cyclization of diethynylbenzene. Paper presented at the 86th annual meeting of the Chemical Society of Japan, 27-30, March 2006.
19. (a) Taduri, B. P.; Ran, Y. F.; Huang, C.-W.; Liu, R.-S. Platinum-catalyzed aromatization of endiynes via a C-H bond insertion of tethered alkanes. Org. Lett. 2006, 8, 883-886;
20. (b) Taduri, B. P.; Odedra, A.; Lung, C.-Y.; Liu, R.-S. Platinum- and ruthenium-catalyzed aromatization of endiynes via intramolecular nucleophilic additions. Synthesis 2007, 2050-2054;
21. For a review, see (c) Liu, R.-S. Catalytic transformations of terminal alkynes by cationic tris(1-propazolyl)borate ruthenium catalysts: Versatile chemistry via catalytic allenylidene, vinylidene, and π-alkyne intermediates. Synlett 2008, 801-812.
22. Vedejs, E.; Steck, P. L. Unusual oxaphosphoranes by acyl transfer from o-acetoxy-o′-diphenylphosphanyltolane. Angew. Chem. Int. Ed. 1999, 38, 2788-2791.